766-46-1

Basic information

• Product Name: 1-BROMO-2-ETHYNYLBENZENE
• Synonyms: 1-BROMO-2-ETHYNYLBENZENE;2'-BROMOPHENYL ACETYLENE;2-BROMOPHENYLACETYLENE;Benzene, 1-broMo-2-ethynyl-;2-Bromophenylacetylene 97%;1-BroMo-2-ethynylbenzene 95%;o-Bromophenylacetylene
• CAS NO: 766-46-1
• Molecular Formula: C₈H₅Br
• Molecular Weight: 181.03
• Product Categories: Aromatic Halides (substituted);Aromatics Compounds;Aromatics;Alkynyl;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 766-46-1.mol
• Article Data: 44

Chemical Properties

• Boiling Point: 92-93 °C20 mm Hg(lit.)
• Flash Point: 147 °F
• Appearance: Colourless Oil
• Density: 1.443 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.231mmHg at 25°C
• Refractive Index: n20/D 1.595(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Acetone, Dichloromethane, Ethyl Acetate, Hexane
• Stability: Light and Temperature Sensitive.
• CAS DataBase Reference: 1-BROMO-2-ETHYNYLBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-2-ETHYNYLBENZENE(766-46-1)
• EPA Substance Registry System: 1-BROMO-2-ETHYNYLBENZENE(766-46-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: NA 1993 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 766-46-1(Hazardous Substances Data)

Usage

Description

1-Bromo-2-Ethynylbenzene (BEB) is a haloalkyne characterized by its colorless oil appearance. It is known for undergoing Sonogashira coupling with methyl 2-iodobenzoate to form bromo tolane derivatives.

Uses

1. Used in Organic Synthesis:
1-Bromo-2-Ethynylbenzene is used as a key intermediate for the synthesis of 1-(2-bromophenyl)-2-(dibenzo[b,d]thiophen-4-yl)ethanone, which is an important compound in the field of organic chemistry.
2. Used in the Production of Heterocyclotriynes:
1-Bromo-2-Ethynylbenzene serves as a starting material for the creation of heterocyclotriynes, which are valuable in various chemical applications due to their unique structures and properties.
3. Used in the Development of Second-Order Nonlinear Optical Materials:
1-Bromo-2-Ethynylbenzene is utilized as a precursor in the development of second-order nonlinear optical materials, which have potential applications in optoelectronics and photonics.
4. Used in the Synthesis of Unsymmetrical 1,4-Diarylbutadiynes:
1-Bromo-2-Ethynylbenzene is employed as a starting material for the synthesis of unsymmetrical 1,4-diarylbutadiynes, which are important compounds in the field of materials science and organic chemistry.

Synthesis Reference(s)

Tetrahedron Letters, 22, p. 2495, 1981 DOI: 10.1016/S0040-4039(01)92942-9

InChI:InChI=1/C8H5Br/c1-2-7-5-3-4-6-8(7)9/h1,3-6H

Upstream product

• 64-17-5 ethanol 
• 2142-69-0 2-bromophenyl methyl ketone 
• 583-55-1 1-Bromo-2-iodobenzene 
• 74-86-2 acetylene 
• 583-53-9 2,3-dibromobenzene 
• 153140-75-1 1-bromo-2-[(Z)-2-bromoethenyl]benzene 
• 213599-19-0 1-bromo-2-(2,2-dibromovinyl)benzene 
• 7345-79-1 2-bromocinnamic acid 
• 18982-54-2 o-bromobenzyl alcohol 
• 38274-16-7 2-bromo-1-(trimethylsilylethynyl)benzene 
• 1066-54-2 trimethylsilylacetylene 
• 79092-33-4 C₈H₄KLi 
• 6630-33-7 ortho-bromobenzaldehyde 
• 994-89-8 tributylethynyltin 

Downstream Products

• 38399-13-2 2,2'-dibromotolane 
• 870010-41-6 [2-({2-[(2-bromophenyl)ethynyl]phenoxy}methoxy)ethyl](trimethyl)silane 
• 27499-64-5 o-bis(ethynyl)tolane 
• 52889-62-0 2-ethynyl-1,1'-biphenyl 
• 1072448-41-9 4-(2-ethynyl-phenyl)-butyronitrile 
• 1109280-57-0 1-(2-bromophenyl)-3,3-diphenylpropan-1-one 
• 1160367-53-2 methyl 2-{2-[2-(2-bromophenyl)ethynyl]phenyl}acetate 
• 1175077-48-1 (S)-2,4-bis(2-bromophenyl)but-3-yn-2-ol 
• 90408-77-8 α-deuterio-1-bromo-2-vinylbenzene 

Relevant articles and documents

Facile Synthesis of Dibenzotetracenedione Derivatives by Rhodium-Catalyzed [2+2+2] Cycloaddition/Spontaneous Aromatization

It has been established that a cationic rhodium(I)/SEGPHOS complex catalyzes the [2+2+2] cycloaddition of biphenyl-linked 1,7-diynes with 1,4-naphthoquinone and anthracene-1,4-dione. Conveniently, spontaneous aromatization proceeded upon removal of the rhodium complex by passing the reaction mixture through an alumina column, to give the corresponding dibenzotetracenediones and dibenzopentacenediones, respectively, in good yields. The obtained dibenzotetracenedione could be readily transformed into the corresponding dibenzotetracene in good yield. This dibenzotetracene showed blue fluorescence with a good quantum yield, which was significantly higher than those of tetracene, tetrabenzotetracene, and hexabenzotetracene.

Iodocyclisation of Electronically Resistant Alkynes: Synthesis of 2-Carboxy (and sulfoxy)-3-iodobenzo[ b ]thiophenes

The iodocyclisation of alkynes bearing tethered nucleophiles is a highly effective method for the construction and diversification of heterocycles. A key limitation to this methodology is the 5-endo-dig iodocyclisation of alkynes that have an unfavourable electronic bias for electrophilic cyclisation. These tend to direct electrophilic attack of the iodonium atom to the wrong carbon for cyclisation, thus favouring competing addition reactions. Using our previously determined reaction conditions for the 5-endo-dig iodocyclisations of electronically resistant alkynes, we have achieved efficient synthetic access to 2-carboxy (and sulfoxy)-3-iodobenzo[b]thiophenes. The corresponding benzo[b]furans and indoles were not accessible under these conditions. This difference may arise due to the availability of a radical mechanism in the case of iodobenzo[b]thiophenes. The 2-carboxy functionality of the iodocyclised products can be further employed in iterative alkyne-coupling iodocyclisation reactions, where the carboxy group or an imine (Schiff base) partakes in a second iodocyclisation to generate a lactone or pyridine ring.

Synthesis of selenium-containing biindolyls and their Diels–Alder reaction toward the synthesis of heteroannulated [a]- and [c]-carbazoles

We reported the first syntheses of 2- and 3-(2-(benzo[b]selenophen-2-yl)-indoles and their Diels–Alder reactions to furnish six unique annulated benzoselenphene carbazoles. This facile route can be used to synthesize selenium-containing biindolyl derivati